Acetic Acid → (+-)(2R*,3R*)-2-amino-2-methyl-1,3-butanediol acetate

HRID 620524노트

반응식

HRID 620524 반응식
[CH3:1][C@:2]([N+:8]([O-])=O)([C@H:5]([OH:7])[CH3:6])[CH2:3][OH:4].[C:11]([OH:14])(=[O:13])[CH3:12]>CCO.[Pd]>[C:11]([OH:14])(=[O:13])[CH3:12].[NH2:8][C@@:2]([CH3:1])([C@H:5]([OH:7])[CH3:6])[CH2:3][OH:4]

참가 물질

5

반응물 2

HCID 176Acetic AcidHCID 13375425(+-)(2R*,3R*)-2-Methyl-2-nitro-1,3-butanediol

생성물 1

HCID 86741969(+-)(2R*,3R*)-2-amino-2-methyl-1,3-butanediol acetate

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

To a solution of (+-)(2R*,3R*)-2-methyl-2-nitro-1,3-butanediol (20B, 22.1 g, 0.148 mol) in 95% EtOH (150 mL) was added glacial acetic acid (25 mL) and 10% Pd/C (MCB, 2.0 g). The reduction was carried out in a Parr apparatus at 50 psi of H2 during a 48 h period at RT. The catalyst was removed by filtration through a Millipore® filter, and the solvent removed under vacuum (2 days). The viscous, colorless syrup was dissolved in abs. EtOH (30 mL). Dilution with abs. Et2O (300 mL) give a cloudy liquid which was placed in a refrigerator for two days. During this time, colorless crystals formed which were washed with Et2O and dried in a vacuum oven at RT for two days. The yield of (+-) (2R*,3R*)-2-amino-2-methyl-1,3-butanediol acetate was 25.6 g (97%) mp 117°-121°, (C, H, N).

후처리

  1. customThe catalyst was removed by filtration through a Millipore®
  2. filtrationfilter
  3. customthe solvent removed under vacuum (2 days)
  4. dissolutionThe viscous, colorless syrup was dissolved in abs
  5. customEt2O (300 mL) give a cloudy liquid which
  6. waitwas placed in a refrigerator for two days
  7. customDuring this time, colorless crystals formed which
  8. washwere washed with Et2O
  9. customdried in a vacuum oven at RT for two days

출처 및 근거

ORD 기록
ord-bc3f6017e67745a4bee12e7c14ab4e7d
출처 데이터셋
uspto-grants-1989_04
특허 번호
US04820873

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